


South Side

by tiamatv



Series: South Side Swing [1]
Category: Supernatural
Genre: Alternate Universe - Modern Setting, But Really Team Switch Forever, Chicago (City), Chicago Mafia, Enthusiastic Consent, M/M, One Night Stands, Openly Bisexual Dean Winchester, Russian Mafia, Strangers to Lovers, Top Castiel/Bottom Dean Winchester, Unintentional Cuddling
Language: English
Status: Completed
Published: 2020-04-28
Updated: 2020-04-28
Packaged: 2021-03-02 00:42:29
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 12,727
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/23896261
Author URL: https://archiveofourown.org/users/tiamatv/pseuds/tiamatv
Summary: Dean knows he's distracted. He's the street boss of the Chicago Outfit, and he really can't afford to not have his head in the game. He's here to meet the damned Bratva who's been running around his city for the past week, and if he fucks this up Bobby will kill him. Well, if this job doesn't do it first.If only he could keep his mind off the hot accountant from last night.
Relationships: Castiel/Dean Winchester
Series: South Side Swing [1]
Series URL: https://archiveofourown.org/series/1734220
Comments: 62
Kudos: 395
Collections: Mixtape Book Club Podcast - Discussed Fics, The Destiel Fan Survey Favs Collection





	South Side

**Author's Note:**

> sharky boi requested "Mafia AU/One Night Stand," and my brain came up with "Cas and Dean staring at the Millennium Park Bean, very unimpressed." So here we are, with the smuttiest thing I have written in fifteen years. Oh boy.
> 
> Thanks to \\\Laura, Queen of the Damned// ([wearetheluckyones](http://www.archiveofourown.com/users/wearetheluckyones_Laura/pseuds/wearetheluckyones_Laura)) for the thoughtful beta!

Castiel Novak was a sonofabitch, make no mistake.

They’d been dancing around this for a week now. Paranoid asshole kept slipping the tail Dean sent in his direction, because of _course_ Dean Winchester was gonna send a tail in his direction once he got word. Russian Mafia waltzing into town and he didn’t think the Chicago Outfit would sit up? What, just ‘cause the Outfit had always been strong in the South Side Novak thought maybe the Brotherhood could tiptoe through the tulips around Avondale far North and no-one would notice?

That sure as Hell didn’t explain why he was standing here in the middle of downtown Chicago right after sunset, eyeballing the skyline in the shadow of a giant metal art installation that resembled a legume. For one thing, yeah, Bobby was probably the nearest thing Dean had to a dad but not even _he_ could normally force Dean into the fucking Loop, and since the rest of the soldiers had at least that much sense, none of them really wanted to be here either. 

For one thing, finding parking for the Impala was a _bitch._

But here they were, plopped in the middle of one of the biggest tourist areas of the city because Castiel fucking Novak had decided to drop into town, and until they found out if he was here, as Bobby had put it, _“’Cause he’s got a craving for Lou Malnati buttercrust or he’s here on the Novak’s say-so and Gabriel’s tryin’ to play ball,”_ they weren’t allowed to make a lesson of him.

“Isn’t this a _great_ idea?” Charlie went up on her tiptoes and leaned on his shoulder, admiring their reflections in the curved surface of the enormous metal kidney bean stretching far overhead and reflecting the edges of the clouds that were barely visible in the failing light of the twilight sky. Dean had always wondered if it was true that someone had climbed to the top of it, but it was all smooth metal, no seams to be seen anywhere, and it went _out_ before it went in, so how… “Wanna take a selfie?”

 _‘Great?’_ That was one word for it. “Really, Charlie?” Dean growled. “Really, the fucking _Bean?_ ”

His favorite fixer—or at least, until _today_ she’d been his favorite fixer—smirked at him sideways, flipped her scarlet hair over her shoulder and then gave him a peace sign for good measure. And to add insult to injury, took a selfie of herself doing it in the reflection of the Bean. Dean’s face on her phone did not look impressed.

“What? You can’t complain, handmaiden, you wanted neutral territory and no escalation of hostilities, and…” she detached from his shoulder and twirled in a circle on the flat, pale stone of the plaza, arms spread. “You’re telling me the middle of the second biggest and only non-enclosed tourist trap in our fair Windy City isn’t as neutral as it gets?”

Well, _yeah,_ since there was a nonzero chance the Polish branch of the North Side Gang would break the uneasy truce they had with the Chicago Outfit if Dean and his people went after Castiel and his people up past River North. And the Bratva damned well knew better than to cross into the South Side, or at least they should, but… “The Russians are _crazy_ , kiddo, and you’ve heard ‘bout Castiel Novak, right?” He wasn’t even an enforcer, so the rep he had, if any part of it was true, meant that he dealt out the hands that he did for _fun_.

Charlie blinked at him. “I dunno, he seemed nice. He’s very polite.”

He sighed. Charlie was the most neutral party that Chicago had, since pretty much anyone who wanted to deal in most of the Midwest had to go through her or risk ending up, you know, on the FBI Watch List, but Dean had decided long ago that she was also probably kind of bulletproof.

It really didn’t help his mood that Dean was really. Fucking. Sore.

He couldn’t even be that mad about that part of it, what the Hell. Dean really _wanted_ to be annoyed, but holy crap that guy last night. Dean generally topped, with guys. Well, he mostly always topped nowadays, ‘cause he was Dean fucking Winchester. His rep was his rep, and with his broad shoulders and big hands and his height, most of the time when someone wanted to sit on his lap they wanted to sit on his cock. Dean didn’t really have a problem with that, though, he’d take what he got.

It had nothing to do with the fact that his soldiers saw him with the ladies all the time—there was still nothing like a guy’s jawline, his throat, flat nipples and strong thighs and Dean’s hand cupped around two dicks, and when he felt that urge, he went for it. He didn’t hide it, not anymore. Truthfully, if anyone in the Chicago Outfit had anything to say about him being bisexual Sammy would probably fuck them up twice as hard as Dean would have even _thought_ of doing. His little brother took that kind of shit real personal. Probably that time of his at Stanford.

(Sammy would probably also fuck anyone up who thought that him being protective over Dean’s identity like that was all sorts of sweet, but pissing off a too-big-for-his-britches little brother was what being a big brother was kind of about.)

Yeah, okay, Dean did not actually want to be thinking about his little brother anywhere near the same brainpan as he was thinking about the guy last night.

The guy who’d clearly had no goddamned idea that Dean Winchester was who he was, and wasn’t that just something? Girls didn’t recognize him a lot of the time, and Dean didn’t take issue with that, but his pretty face had been a regular at Jeffery Pub since he’d come out and proud. Represent, fuck yeah, nothing wrong with being badass and bi. And for every tourist who came to see the drag show at Jeffery’s, there was another who came to take a peek at the Chicago Outfit’s street boss.

Alleged street boss.

Hey, he was just a mechanic at Bobby Singer’s shop, nothin’ to see here, nope.

Dean couldn’t even pretend that he hadn’t been the one to start it, because he really had. Oh, sure, the guy had been _looking,_ and not in the giggly way that some girls did, peeking and looking away. No, that had been pure naked appreciation across the mostly empty, stained wood of the bar stretched across the wall—a chef kiss given eyeballs, and Dean had just been waiting for the guy to stand up and cross the floor towards him. His eyes were some dark color and his hair the same, he had a hint of shadow across a cut jawline. Fine-looking enough, Dean guessed, with a serious pout of a mouth and all the cookie-cutter style of a businessman in the wrong neighborhood after dark.

Dean had to admit, he kinda liked ruffling that type up a little. Or a lot. He rocked their world, they’d got what they’d come down to Southie for and were grateful, Dean felt good about it and got his cock wet. 

Except… the pretty thing hadn’t come over. Just kept looking.

And by the time Dean was past his second Johnny Walker, well, now he’d just gotten _curious_ , because he could’ve sworn he’d even seen the guy staring in Dean’s direction and _sighing_ , and who even did that? He raised a finger to Smoke and tapped the edge of his tumbler, raising a finger again for a refill—she rolled her eyes at him but wandered over the bottle of Black, topping him up, the faded tattoo on her left forearm flexing.

Dean flicked his gaze in the direction of small, dark and staring. “What’s up with him?”

“That one?” Smoke gave him an amused look down the bridge of her elegant nose. Her shoulders barely moved under her sleeveless black blouse, but she gave the impression that she’d shrugged. “Didn’t think he’d be your type, pretty boy.”

Smoke Thompson had been one of the first people he’d come out to, right here, so she’d probably know a little about his type. Dean raised his glass to her, then gestured to an empty shot glass. Smoke laughed and poured herself a drink, and Dean leaned an elbow against the bar and clinked glasses with her. “What type is that?”

She smirked. “Well, you like ‘em slick-tongued and charming like you, don’t say you don’t, Dean—and he sure as Hell can’t talk to girls.”

Yeah, in the time Dean had been sitting here nursing his drinks, he’d seen a girl just out of her tweens go over there and walk away muttering something about ‘who talks about someone’s _father?_ ’ and the sweet middle-aged lesbian couple who came for a drink every Wednesday had tried to talk to him and then kind of stopped trying. Dean raised both his eyebrows and gestured up and down his body—these jeans weren’t new and his fine ass made broken-in denim look like a choice everyone should make. The battered, scratched leather jacket he had thrown on over a plain white t-shirt was perfect for late Chicago spring, and concealed his holster properly unless he wanted it to show. “I look like a girl to you?”

“You do have very delicate features,” Smoke told him, serious as a heart attack. “You know, for a mobster.”

Just for that, he snatched out across the bar and tugged at the long, curling end of her hair, and she slapped at his hand, cackling. “Oh no you didn’t, Winchester, you are not messing with my weave!”

“What’s he drinking?” Dean demanded.

“Oh no,” she turned her back to him to start messing with bottles. “No, no, no. _You_ deal with the lost townie. If he stares at you any longer his eyeballs are gonna fall out and I will not be responsible for that, I really won’t.” She smirked. “You might change your mind when you see his coat.”

What? Dean ran the tip of his tongue along his teeth and shot finger guns at her, so he probably deserved it when rather than handing him the key to the back room she tossed it at his head. Almost got him, too. Wasn’t a good sign that she’d been throwing things at him long enough to get good at hitting him.

Dean led with his swagger and watched the eyes get bigger as he approached, and by the time he was halfway there the little accountant was looking around him as if there could possibly be anyone else Dean was walking for. Dean waited until the guy’s gaze crossed over him again, then put on a slow smile, and his eyes stuck on Dean’s lips like Dean had hooked them. 

He still didn’t say anything, though, and after a moment, Dean chuckled. Alright, so maybe Smoke hadn’t been kidding about the problems with the talking. “Hey, man. You here to look or you here to play?”

“I’m sorry, I didn’t mean, I’m just…” The guy was clearly embarrassed, but he peeked up at Dean through eyes like dusk over Lake Michigan in summer. “I’m sorry. I’ve been very rude.”

Dean was already blinking back down at him anyway, because all right, he had _not_ expected a voice like that out of an out-of-place accountant dude with hair he’d clearly been running his fingers through. Well, now, _wow_ , hello whiskey and spice, like a hot toddy with too much Jameson in it, just how Dean liked it on a really cold day.

“S’okay. I’m adorable. I get it.” He grinned, and propped his hip lightly at the edge of the bar, looking down at a man looking up at him like he wanted to put his mouth right on Dean’s hipbone, and sure, he had a meeting with the Russians who’d been fucking around his city tomorrow, but right now, there wasn’t anything better than this. “You didn’t answer my question, though.”

That got him a long, slow blink, and just as Dean was wondering if maybe he _had_ misread, the guy said, shyly, “May I buy you a drink?”

*_*_*_*

Dean wondered for just a moment if he was maybe being too rough when he shoved the guy against the wall with one hand so hard his shoulder blades thumped against it, and kicked the door closed with a foot at the same time. It was a feat of coordination, truthfully, but he'd done it so often it was easy. (So… maybe he did do this a little too often, but he was always safe and everyone had a good time, so why the Hell not?) But the guy just made a small, low sound, not a growl so much as a moan in another octave, and reached out for Dean.

The soft yellow light of Jeffrey Pub’s back room was really fucking flattering to Dean’s awkward-cute businessman, and Dean stopped and stared for a second, ignoring the hand clutching at his shoulder. _Damn._ He’d liked the guy’s voice, the way he’d blushed warm and shocked when Dean turned on the charm, the way he hadn’t quite known what to do with his hands when they talked. It wasn’t really what he went for, not normally—but Dean’d already been looking forward to the rest of the night, ‘cause that’d all been a sight cuter than he’d thought when he’d first caught sight of him across the bar. Not an asshole, either—not afraid to meet Dean’s eyes, for sure, kind of dry and stumbling, maybe just a bit boring. Had never seen _Star Wars,_ seriously? Had _no_ idea how to make conversation, for all his looks. But he’d tipped Smoke well and hadn’t thought there was a sure thing here, looked surprised and grateful and just as pleased as punch when Dean invited him back just as they tipped back the last of their drinks.

The half-light in the bar hid a lot of flaws, and that was _why_ it was in half light, that was what a bar was about. But with all of those features clearly visible now it was pretty clear that this guy had nothing to hide. In full light he was even prettier—cheekbones to cut with, a dimple in the middle of his chin that looked darker with just that ideal hint of scruff: Dean could already imagine that rasping against his face or the tops of his thighs. He had hair that wasn’t just messy but was dark and inky, thick enough to grab onto, and pouty lips that were so much more pink now. Nope, not a twink or a daddy, maybe he was somewhere about Dean’s age, with a few lines in his forehead and some crow’s feet giving the pretty face some character.

And those eyes. Dipped down at the corners, big and a little sad, a dark, intense blue with a dark, intense look that skittered down Dean’s spine. Fuckin’ _wow_. Those eyes went with that voice right onto Dean’s kink list.

Not his type? He didn’t know what the Hell Smoke had been thinking, Dean was just about _dying_ to ruffle him up.

The first kiss was always a gamble. Dean knew it. He’d backed out of more than one encounter just on the force of that, because he found bad kissing a _real_ turn-off—lips that didn’t know when to tighten and when to relax, a tongue trying to gag him, or, ugh, someone trying to lick his face, _gross_. Especially when it was a guy, and they were being either too aggressive or too squishy—Dean couldn’t always say for sure when there was a closet situation involved (though with the staring, if this guy was in the closet he was peeking out of it more than he maybe should be.) He didn’t even always kiss, Dean was honest with himself about that, sometimes it was just skin and slick, hands and cocks. But the way his new friend was staring up at his mouth with parted lips and a desperate look, well, not giving him what they were both wanting would’ve just been a shame.

He didn’t kiss shy, either, when Dean leaned in and stuck a hand between short, thick dark hair and the wall, the better to guide him just how Dean wanted him. His tongue was a careful little flirt against Dean’s bottom lip before Dean demonstrated on him just how he liked to taste, his lips were so, so _soft_ , chapped in the way of someone who’d been licking at them all night. He had his eyes closed and his head leaning right into the cradle of Dean’s hand when Dean finally pulled back, breathing hard, that fucking obscene mouth still hanging just a little open like he was inviting Dean’s tongue right back in, thank you.

Hell, Dean nearly went, but there were other places he wanted his mouth to be tonight. He dropped a kiss on the corner of that tempting mouth instead, and they were so close he saw the way those dark eyelashes clung together as his little accountant’s eyes drifted back open.

Well, not so little after all, it turned out. Dean had blinked when he’d stood up from the bar stool—but he kind of liked that too. Liked being on the same level, sometimes, the same way he liked strength as much as soft.

“Yeah…” Dean breathed, pulling back, feeling his eyes heavy and his hands shaking a little. Oh, he was looking forward to this for _sure._ Then he blinked, thought. Laughed. “Y’know, did we even trade names? I’m—”

Blue eyes flashed at him, eyebrows tipping together in irritation, and to Dean’s outright shock he found a hand jammed up between them, palm pressed across his lips, holding back the name. “Don’t.” The command in that gravel almost raised Dean’s eyebrows. “Don’t do that.”

Huh. Closet? Maybe Dean should’ve been offended. Instead, he laughed into the rough palm resting on his mouth. He couldn’t even have said why he was amused rather than annoyed. Maybe it was because the palm wasn’t gonna keep him saying anything he didn’t want to, it wasn’t that kind of pressure. 

He didn’t lick the hand on his mouth the same way he would’ve if someone he knew had done it, didn’t break a finger the way he would’ve if it was someone he didn’t. “You don’t wanna know or you don’t care?”

The guy scowled, and shook his head sharply. “You weren’t going to give me a real name anyway, so why should I want to hear it?”

Dean blinked. That was… maybe true. Maybe. Okay, probably. ‘Michael Wesson’ had had more than one run through this room before. Just ‘cause people knew who he was in this part of town didn’t mean Dean had to be stupid about it. 

Dean flicked a fingernail hard at the inside of the wrist near his mouth, hard enough to sting, and this time the guy lifted his hand away, still frowning. Dean drank in breath, no aftershave or cologne there, just the smell of fresh-laundered cloth and sweat and… was that gun oil? No, probably just his imagination, that, but fuck, his mouth was _watering._ He liked a guy who didn’t cover up what he smelled like. “What’s wrong?” he teased. “Wanted something to scream?”

“No. I just find it very offputting when I’ve gotten someone so ‘distracted,’” Dean’s mouth fell open—were those fucking _air quotes?_ “that they forget which name they are supposed to be responding to.”

Oh, this _guy_ . Dean didn’t know whether to gape or laugh or bend him over the table or drop to his knees and blow him. Couldn’t remember the last time he’d wanted to laugh like this, much less with an awesome creature like this looking up at him like he didn’t give a damn that Dean had a couple of inches on him and was pressing _him_ into the wall. “Goddammit,” he finally chuckled. “I like you.”

Those bold, blue eyes narrowed like he thought maybe he was being mocked—he was, but that didn’t mean that Dean didn’t _mean_ it. “Good,” he answered, seriously. He lifted his chin, and the pride there was something to see, oh for sure. He nodded towards the bed, over Dean’s shoulder. “I would like you on your hands and knees tonight, please.”

Holy. Fuck. _Well_ then. Dean didn’t know if it was the ‘please’ or the fact that the world’s fucking sexiest nerd clearly expected Dean to strip and _do it_ , but he almost did. Right then, he almost did.

Instead, he leaned in, let his weight carry them further against the wall, chest to chest. The guy’s lips parted, his legs tipped apart, and Dean nudged his knee between them, felt the rise of muscle against his thigh—mmmm. “Yeah?” he purred, and let the hand that he had resting on a tight waist slide downwards, grabbing through pants and… okay, that was _muscle_ under his palm, a firm round globe of an ass, the kind it was a crime to cover up in polyester. “What if I don’t bottom, pretty boy?” 

Not true, not even slightly true, but it _had_ been awhile—a long while. And those thick thighs, Dean could see those wrapped around his waist _easy,_ maybe if he was flexible enough one knee thrown over Dean’s shoulder to hold him wide open as Dean bottomed out in that perfect ass… _mm_.

The guy raised his eyebrows, but he didn’t blow a toppy gasket. He just shrugged, and let Dean lean in to press a kiss to the side of his throat. His eyes drifted half-closed and the line of his neck was perfect vulnerability, topped like a cherry with an Adam’s apple to match that fuck-me voice. “Alright, then,” he murmured. “I’ve no interest in fucking someone who doesn’t want to be. Backing myself on your cock would, I’m sure, be no hardship. Or perhaps I could ride you?”

Dean wasn’t even walking, wasn’t even moving to do anything but maybe put his tongue right on the ridge of that Adam’s apple, but his brain stumbled and laid itself out flat, and he looked up. Fuck, _fuck_. “Huh,” he managed, caught up in that thought, too. “Just like that?”

“Just like that.” He glanced sideways, and snorted at whatever expression was on Dean’s face. “I very much enjoy that too, and don’t see the point in us pretending we don’t have parts that can go both ways.”

Dean really, _really_ liked this guy. “Damn,” he breathed. He’d challenge anyone who didn’t find that kind of confidence, that kind of _acceptance,_ just as sexy as the eyes and the voice. “You an angel or somethin'?” Or a demon, maybe. Shit, he was feeling really damned sorry he was probably only gonna have him for a night, ‘cause Dean wasn’t a teenager anymore and it’d been bad enough when he’d only had _one_ non-interchangeable set of visuals running through his head.

That one danced on a nerve, got him a frown. “No.”

But he didn’t say anything more, just looked Dean up and down like Dean was a popsicle he wanted to lick—waiting for _Dean_ to make that call. Dean’s tongue flickered out to wet lips he’d forgotten to wet sometime in the last few _hours,_ and his gaze followed that, too, patient and appreciative. “ _Well,_ then. Y’know. I _don’t_ bottom much, but… I’m… pretty sure we can work out a deal,” and Dean’s voice wasn’t as deep or as raspy as this okay-not-an-angel’s, but it was sure getting there.

A perk of enthusiasm. If not for the fact that Dean was pretty sure he could not shut his own mouth up at this point, they could probably have a whole conversation just from the crinkles in the guy’s eyes, the purse of his lips and the way he cocked his head. “Can we?” he inquired, inclining his head to the side like a little bird. “I think you’re used to getting your way. I’m not sure you’re going to behave.”

“Yeah?” Dean smirked, and leaned in. “Well, then. Make me want to.”

Yeah, yeah. That was an inside joke. While Dean didn’t think he was a bad guy—even with what he did with his life, just ‘cause a lot of it was illegal didn’t mean it was _bad_ —he wasn’t ‘zactly what anyone with half an eyeball in their head could call ‘well-behaved,’ and he certainly didn’t _want_ to be.

Blue, blue eyes widened just slightly, then flashed at him like a camera going off. Dean had about half a second to think that this could be a bad idea or this could be _awesome_ when the pretty boy murmured, “I can do that,” and his hands grabbed Dean by the collar.

Dean was the street boss of the Chicago Outfit. He’d been getting in and out of scraps since he was a walking scrap himself. He was good with his gun but an artist with his fists, his legs and back and arms heavy with the evidence of it, and absolutely none of that explained why all of a sudden a leg had hooked between both of his, an arm slammed against his other shoulder, and _twisted_. Then his back was jammed against the wall and an accountant in a pout and a suit and badly tied tie was holding him against it with one firm forearm pressed lightly against Dean’s collarbones. 

Dean would have gaped, but said pouty accountant’s other hand was popping the button on Dean’s worn jeans.

Dean had told this nerdy little guy to make him want to behave. Mostly for laughs. And yeah, the guy had _said_ he could. Everyone always said that. Everyone thought they could.

But he’d said it like he _knew it_.

By the time he had those perfect pink lips stretched around Dean’s cock and his nose pressed all the way against Dean’s belly, Dean was fighting to stay up against the wall because even with the condom on the feel of a throat around the head of his cock was fucking _irresistible_ , and he had to kind of conclude that… yeah, maybe he _really_ _could_. 

*_*_*_*

_“Where the Hell are they?”_

_“How am I supposed to know, maybe the Red Line’s running slow.”_

_“Charlie, the Pakhan of the Russian Mafia is not going to be taking his people on the CTA to a fucking_ _mob meeting_ _.”_

_“Well, how do you know? He might be environmentally conscious.”_

*_*_*_*

Dean really _liked_ unwrapping his presents, and that went for all kinds of presents. He knew it didn’t always mean that he was gonna like what was inside them, but that wasn’t the point at all anyhow. Sure, Dean liked a nice set of curves on a girl and shoulders to balance his own out on a guy, but there was all sorts of fun to be had with all kinds of bodies. And undoing a twisted navy blue tie that wasn’t even snugged up against his throat—and it was a square knot, who’d tied this thing, his pet cat?—and tugging a white dress shirt out of where it'd been tucked crumpled into the top of black slacks was nearly as much fun as getting his hands on what was inside them. 

They were kissing hard enough to bruise now, Dean so turned on his whole groin was throbbing, since he’d pushed his new friend off before he’d come. Dean had almost shot off anyway, and had to grab at the base of his cock to keep from doing so, because even with Dean’s hand in his hair his businessman had tried to struggle closer again, face pink with effort, mouth already open, tip of his tongue resting against his bottom lip. 

So hungry for another lick. _God_ . No doubt he wanted it. No doubt he _loved_ sucking cock. How’d Dean get this lucky again?

But there’d been no coordination left after that sight. It’d already taken _way_ too long for Dean to wiggle out of the pants he’d had bunched and tangled on top of his boots.

So he wasn’t paying maybe as much attention as he ordinarily would have when he impatiently shoved the mess of shirt and suit jacket off his businessman’s shoulders, because Dean had his tongue in that soft, hot mouth, and apparently he could suck tongue just as well as he could suck cock.

And then he realized what his body had been yelling about even though his brain hadn’t even registered. Dean had to stop and do nothing _but_ pay attention, because. Whoa. _What?_

The pretty-boy was squinting up at Dean like a silent demand of why he’d stopped short, with both shirt and jacket crumpled on the floor. He had not a single fleck of chest hair, small, flat dark nipples, a slant between neck and jawline that was just made for hickeys. He also had shoulders set tight and hard with muscle, collarbones that should’ve come with their own archery range, the deep triangular groove of his hips was a reading right out of a book of erotica, and he had a delicate fucking _six-pack_.

And peeking out of the open button of his slacks was what looked for all the world like a pair of tightie whities, which _should_ have been a completely dorky turn-off but instead was kind of like Calvin Klein was bringing sexy back and by damn they should all know it.

While Dean was still staring, the guy who had yet to stop surprising him at every single turn shrugged, and pulled the rest of his clothing off with a simple, smooth casualness that left every muscle moving in just the right way. It would have been mouth-watering even if he hadn’t looked like _that_ under the suit. Dean had made a lot of fun of yoga and pilates and Zumba or _whatever_ in his time, but right now he really wanted to put his money where his mouth was, or maybe his mouth where his eyes were, and those actually _were_ tightie whities being pushed down heavy thighs dusted with just a bit of dark hair, and—

Whoa. Also? Not circumcised, and the way the guy thumbed back his foreskin, easy adjustment with a flick of his thumb like he had no idea how hot that looked… well now. Dean didn’t even have a kink for that kind of thing the way that he knew other guys did, but all the same, _that_ wasn’t a treat that Dean often got here in the middle of the Midwest, either.

Those blue eyes met his, narrowed at the corners with the intensity of his look now, and he didn’t let go of his own cock, but tipped his head to the side as if inviting Dean to look. Which Dean was. Oh, he was. Except, then, “What?” he asked, like he had _no idea_.

Dean meant to say something charming. Admiring, even. This guy was a _gift._

Unfortunately, the noise that Dean made probably meant something in some language, but it sure as Hell wasn’t English.

Hot Stuff blinked like a sexy, naked, confused owl.

“You’re a sexy, naked, confused owl,” Dean’s mouth said, seriously, with no input whatsoever from his brain.

Wait, what? _Fuck_.

Dark eyebrows bunched up on Hot Stuff’s forehead. “ _What?_ ”

He didn’t know which of them started laughing first, but they both were, deep crinkles appearing beside those pretty blue eyes, the corners of Dean’s mouth tight with amusement in a way he couldn’t remember them being in awhile. He did know that when they both stopped snickering, though, when Dean walked forward, not even sure what the Hell he was going to do other than that he was going to _touch_ , he wasn’t the one whose arms came up first, whose fingers were the first to grip into the bare muscles of his back and press close, fitting them together in a slip slide of two guys really close to the same height whose dicks had just gotten _really_ friendly.

“If this is you behaving, I’m _concerned_ ,” the dorky accountant who’d suddenly morphed right into a hot bodied _sex god_ murmured, and what had been a hot toddy of a voice before was pure _whiskey,_ now, full-proof and foolproof, and Dean was totally in the mood to get drunk on it. 

*_*_*_*

_“Do you think Gabriel’s going to play ball?”_

_“I dunno. Lucien Novak was a fucking dick with a doubly pretentious fucking nickname, and until I hear any different ‘bout Gabriel I’m shooting first. Again. Like Han. Yup.”_

_“I… yeah. Don’t… yeah, don’t do that. Not the Star Wars joke—no, I… okay.”_

_“Breathe, Samantha.”_

_“Fuck you. Look. I know it was bad, Dean, but—”_

_“But fucking nothing. No, Sammy. Yeah, this life sucks sometimes, but_ _no._ _I only shot ‘im through the knee ‘cause I didn’t have a good line at his head without hitting_ _you_ _.”_

_“Gabriel kicked him out for that, though. A whole takeover. I have to believe—”_

_“So that means he can’t be just as bad?”_

_“I’m just saying. You shot Lucifer, and there was no retribution. Gabriel even sent his little brother this time. I know they call it the Brotherhood, but this is his_ _actual_ _brother.”_

_“Yeah, and so was Lucifer and he’s rotting in some cage in, I dunno, Siberia or Hell or something now. You don’t know that Castiel Novak’s here to talk and neither do I, Sammy, ‘cause coming into our city without acknowledging us? That don’t feel like ‘talking.’”_

_*_*_*_*_

It’d been a long time since Dean had had someone else’s fingers in him, and he’d forgotten that it could feel so different from his own. It wasn’t a matter of girth or anything, a finger was a finger, but it was a matter of angles. Of contact. Of not knowing exactly what kind of touch was going to come before it was here, or there, or _right there_.

Ass up and face down, with a big and surprisingly callus-rough hand resting on one ass cheek and a thumb holding him open, Dean breathed through the first easy, wet slide of it, relaxed when the press in paused with just a fingertip inside. He normally liked to open himself up even when he _did_ bottom, this was the kind of thing he normally didn’t trust anyone else to get right but himself, but there was just… something here. Maybe it was knowing that this guy liked to bottom and so probably knew what it took to get someone warmed up right.

Maybe it was the way he’d dropped kisses down Dean’s back and shoulders and pressed his thumbs slow up the back of Dean’s thighs, his palms and fingers cradling the big muscles on the sides, stroking his hips, easing into the touch before he went for either cock or ass. Either he didn’t do one-nighters much—which was almost definitely the case, considering that Dean had had condoms and lube on hand, Hot Stuff hadn’t, and his embarrassed blush when he’d had to ask for them had been _really cute_ —or he always took his time, and either of those, well. Hey, Dean had no problems with any of that. It was… kind of nice being taken care of.

He definitely had no problems at all with the way he was feeling around right now—just the very tip of one finger in Dean’s ass, not going any deeper, and it wasn’t ‘cause he was feeling shy—not with the way he was slowly pulling and tugging at just the rim’s muscles in a way that felt tingly and expert and unbalanced and really, _really_ nice. Even with how impatient he was feeling to just be _fucked,_ Dean felt his throat vibrate in a low noise of appreciation. Yeah, _very_ different.

Dean twisted a little to watch his guy, grinned lazily at the concentration on that face, the way he had his eyes narrowed in thought and his lips pressed tight together.

“You’re very tight,” Blue-Eyes noted, catching Dean looking at him. He didn’t look worried about it, though, just thoughtful. His finger pressed a little deeper, his knuckle catching just barely on Dean’s rim, _mm_. Yeah, this playtime was awesome, but Dean was ready for something a bit more serious.

“Why’re you sayin’ that like a bad thing?” Dean grinned wider, and clenched around the fingertip inside him just to see the way it made that intense concentration shiver around the edges, and his little businessman had to stop and take a couple of deep breaths to get himself under wraps, oh this was gonna be _great_. 

“It’s not.” His other hand stroked the small of Dean’s back. “But I would like you to enjoy this.”

Well, that was sweet, and Dean almost chuckled again—how was this guy even _real?_ But he pressed his own hips backwards, impatient. That got him a bit more, in and _in,_ that finger was long and slender but it had to be almost all the way in now, he could feel the teasing brush of the rest of his fingers against his sensitive crack… but not enough, and dammit, he was doing that stretching thing again, just deeper, pressing and curving a little—

“Hmm. How is this?”

 _Oh_.

Dean jolted forward on the bed and almost unbalanced onto his own face.

“Do you enjoy prostate stimulation?” Dean was still choking for voice and trying to get his arms back underneath him and his elbows supporting his own weight when that finger swept sideways, across, then returned to the middle and _pressed_ , careful still, but milking across him in a slow slide. “Not everyone does, there’s no shame in—”

 _“Yes,”_ Dean groaned, and gave up on trying to hold himself up. “Yeah, I… yeah.” He kind of wanted his angel to stop talking, except he didn’t really want him to stop talking at _all_ , and he reached underneath himself rub the heel of his hand on where his cock was dripping all over the sheets, just to take the edge off the dull heavy throb of want. If he stroked himself this was gonna be over too soon—but no sooner had he cradled his poor aching cock in his fingertips than long fingers wrapped around his wrist, dragging his palm gently back to the sheets.

“Can you come just from it?”

Dean whimpered and considered it, his hand flexing empty. He really did. Or at least he considered it as much as his brain could consider anything right at this very moment, with those small, slow beckoning motions inside like he was getting the pleasure slowly petted right out of him. Finally, regretfully, he shook his head. “Don’t… don’t think so.”

He heard the little nod as much as he felt the motion of it. Which was why he didn’t expect the “Would you like to try anyway? I enjoy it, myself.”

“Oh _God_ ,” Dean breathed, buried in the sudden _visual_ of that, pretty-boy tousled and shattered with his knees to his chest and coming wet all over himself.

“Don’t blaspheme,” and he said that so fucking absently that Dean couldn’t even—he couldn’t, and he just shuddered, instead.

He’d never been opened up so slow, there was barely any burn at the second finger, none at all at the third, just that electric feeling of _stretch_ . “I’m ready, come _on_ ,” Dean wanted to think that his voice sounded like a growl right there, but it probably didn’t. His nails skidded on the sheets when his hands fisted, relaxed, fisted again as three fingers inside him covered a surface area that felt like thirty percent of Dean’s entire body.

“You’re not.” The soft snap of the cap flicking back open shivered down Dean’s back, and he arched, hissed as his angel trickled lube down his crack. It wasn’t cold, but the slick of it was slipping _into_ him between slender, spread fingers, and the sloppy noise it made when those fingers pushed all that wet back into him would have made Dean more red if he’d had any blood left to go anywhere but his cock. “See? You tightened, just there.”

Yeah, because half of his nerves had just relocated to his _rim._ “ _Fu-uck_ ,” Dean breathed, and pressed his face into his arms. “I am, I seriously… C’ _mon_ , man.”

“You’ll be sore,” the sex god behind him warned. Then, with a shaky little tremor of a laugh, “You are so… I don’t… I don’t know how much control I have.”

Could have fucking fooled Dean. The truth gasped out between his clenched teeth. “I _wanna_ be.” 

That got him a sharp inhale of breath behind him and the fingers inside him curled, and this time Dean wasn’t sure that it had been intentional but holy God he’d take it and take it _good_.

Yeah, he wanted to be feeling this. Wanted to carry this with him, a day or two—slow, stubbly kisses against the wall, blue eyes crinkled with shy laughter, this guy being so damned careful about Dean’s pleasure even when his own cock was so hard his glans was bright, lollipop red through the pale film of the condom. Shoulda sucked him, felt that weight on his tongue, made him wheeze as Dean licked under his foreskin. No time for that now.

And, yeah. Yeah, the catch of a cockhead right on his stretched-out pucker was almost good enough by itself to make him keen, oh God, but the next long thrust into him—careful, but not slow, not gentle, not at all—almost whited out the inside of Dean’s brain. His cock bobbed and dripped in time with the little jerking, quivering motions of his ass adjusting around… _Jesus_ that ached, he was big, but with all that prep it was really fucking good—Dean hadn’t even known he’d get this tonight. But even with Dean’s body fluttering around him he _didn’t stop_ , and Dean didn’t want him to, oh God.

“ _Ah!_ ” and Dean wasn’t sure which of them made that noise, high and bright and shocked. There were hands on his hips as they bottomed out together, the press of firm legs and cut hips against Dean’s thighs and ass just completing the circuit. Dean breathed into it, deep, he couldn’t get enough oxygen and he didn’t even _care_.

So yeah, he might’ve shoved back just a little to get just that tiny bit _more_ , his body squeezed tight and Dean wasn’t even sure if it was protest or just to hold and _pull,_ and behind him, his sweet, bossy little accountant moaned. It was deeper than deep, it sounded like _he_ was the one getting fucked out, and there was something so damned good about that, too, electric and symmetrical, like Dean wasn’t the only one being wrecked.

Yeah, maybe he was gonna regret this, mind was willing and all but it really had been way too long and he should’ve given himself more time to just sit with it—sit with all of this and let his body adjust. Dean wasn’t relaxed yet, couldn’t relax with how full he was, and if he didn’t he really was gonna be sitting sideways tomorrow—but there was a forehead resting between his shoulder blades, his angel was panting little kisses across his spine, and the hands on his hips were _shaking._ “Oh… oh, you are so…” he gasped, barely words. “May… I?”

Really, there was only one answer to that.

“Hell, _yes_.”

The next thrust was short and sharp, not quite testing but definitely not gentle, and the motion of it was with his whole body—abs and chest sliding up Dean’s back, so close—slippery and hot inside him and the lips were at the back of his Dean’s neck, now, a hot ruffle of short hairs. _“Fuck—”_ fell out of Dean’s lips, because that next roll of hips nailed right where Dean thought he might even be a little too sensitive now. He _felt_ the way his whole body jerked upwards and heat dribbled up and out and rolled off his cockhead in thick trickles. Jesus, what _was_ he—

He didn’t stop. One after another, pounding into him, Hell. Dean was _begging_ him not to stop. He thought it was just in his head, first, _Yeah, yeah—just like that_ —and when he realized it wasn’t just in his head at all, pressed the words into the thin pillow under his mouth, bit down wet.

“Don’t—” behind him, some of the weight left his back, a hand yanked at his left shoulder. “Don’t hide.” Maybe it was a command. Maybe it was a plea.

This was too damned much, it wasn’t at all what Dean had been looking for when he’d caught a pair of blue eyes staring across the long bar at Jeffrey Pub, couldn’t have known what he’d get when pink lips parted in amazement at Dean’s _“Hey, I’ve got a place, wanna--?”_ Maybe it was all the foreplay, maybe they’d _both_ been impatient, and there was something good about that, too. He’d been looking for a fun way to play, gotten _really fucking intense_ instead, and… he hadn’t even known he’d wanted this.

‘Cause he did. He really, _really_ did.

He barely kept his balance as he reached up and pressed a hand onto the fingers on his shoulder, pulling himself just barely out of his own head. Could only keep it there for one press of skin to skin because the next thrust into him was hard enough to rock him forward, and he slammed that hand into the wall to shove back into it.

“ _Oh,_ ” Dean didn’t know who was in control here anymore, because it really wasn’t Dean, but it might not be his not-at-all-an-angel either, and there wasn’t any room in his brain for any of that. He had the rhythm of it, now, the slick high burn was gone and the ache was deeper, so _deep_ , convulsing through the bowl of his pelvis with every thrust, every dirty little press and roll. Teeth printed his shoulder blade in a bright flash and his hips jerked and he was _so close_ , so fucking close, he’d really never come just from something in his ass before but he thought—he thought maybe—all he needed—

The groan behind him and into his back was low and wordless and the way the thrusts into him quivered and all of a sudden he maybe felt even a little bit _bigger_ as he twitched and jerked, keen as the way his fingers had felt curling—yeah, all that was as eloquent as a scream. And as gorgeous as the weight slumping onto his back felt Dean wanted to cry because _fuck no not yet not yet_ he wasn’t ready for this to be over—

Then a callused hand came around, petted loose around him once, and Dean grabbed hold of sheets, lost it, lost himself. Painted his own chin with his come.

*_*_*_*

Dean normally did like talking a bit after sex. Hey, how are you, that was awesome, huh? He liked to check in. But he couldn’t get his head to move in that direction. His ass ached, empty and throbbing now, he really was gonna be sore, and he was gonna love every step of it.

Maybe the silence in the room should have been uncomfortable, just breathing and skin, but it just… wasn’t. Besides, even if it had been there really wasn’t anything he was gonna be able to do about it. Yeah, it was gonna take a hot minute to retrieve Dean’s brain from where it’d gotten launched into space somewhere. 

Jesus.

His lips made the syllables but they didn’t make it out. The just slightly hysterical giggle as he imagined getting ‘Don’t blaspheme’ mumbled into his neck, where there was a mouth and a nose nestled, didn’t quite make it out either.

Hey, he’d challenge _anyone_ to have any sense left after, well, that. Okay, no, he hadn’t quite made it into coming without a hand on his cock, sure. In the end he’d needed just one good long stroke as his angel moaned low and shaky against the back of Dean’s shoulder and his hips stuttered, but just the _one,_ holy shit. 

With a bit of practice—

Wait, what? Where’d that come from. Dean might be feeling wrecked and empty and so fond it hurt _now,_ but he’d picked up a pretty stranger at a bar and pulled him into the Jeffrey Pub back room he used for just this kind of thing. He didn’t even know the guy’s name and Dean Winchester was fucking _Chicago Mafia_ . Of course there wasn’t gonna be any _practice._

Dean shifted on the damp sheets, suddenly uncomfortable.

His dorky businessman sighed, softly, like maybe they’d had something like the same thought—which, of course, they couldn’t have, Dean noted a little wryly. But he tugged and rearranged them both until he must have been on the very edge of the bed. Yeah, this was it, this was where they unmolded from one piece into two. This was Dean’s least favorite part of this even at the best of times, but…

But the guy behind him sighed, and rather than twisting to get off the mattress, he pressed against Dean’s back, one hand molding to Dean’s belly where it was getting just a little soft from one too many pieces of pie, and… what? His thumb stroked lightly at the tiny patch of fur just south of Dean’s bellybutton, tickling, a bit of a rasp. Dean was still so boneless it took a couple of seconds of the breathing slowing again behind him before he even realized what this was.

“You… wanna _cuddle_?” Dean asked, incredulous, twisting to glance backwards.

A peek of sleepy blue eyes over his shoulder. “Yes…?” he started, simply, before his expression went flat with uncertainty and his inflection tipped up at the end. “Can we? Just…” a tiny hesitation and his gaze dropped. “A few minutes.”

Shit. Dean knew he was an insensitive bastard sometimes, but even _he_ knew that had been really intense, and _he_ didn’t even want to move, so why was he questioning it?

Because getting attached was a bad idea?

Might be too fucking late for that, though.

“Uh… well, um. I guess. Okay.” Dean shifted his hips, tipped to the side, straightened them out. Checked his fucking insecurities at the door, what the Hell, Winchester, it wasn’t like he’d ever tell anyone or have anyone to tell, he wouldn’t get this again, so why _not_ have it now? Then, as knees pushed gently behind his and they curled together, he murmured, “Sure,” the way he’d kinda sorta already wanted to, and felt a small puff of relief, a press of lips against the nape of his neck. Felt the eyelash flutter of a startled blink at the back of his head as Dean carefully reached up and put a hand over the warm one resting on his belly, nesting their forearms together.

But it was the almost-soundless little “Thank you. I wish…” and then a soft little sigh that kind of turned his belly to pudding. He trailed off into “Thank you,” again.

Dean kinda knew, though. He let the holding happen. Melted into it for minutes, maybe an hour, until he was floating sleepily in the barely audible sounds of the bar closing up, until he could feel a shift of weight against him, another slow breath. He reached back to run his fingertips down the side of a long, lean, gorgeous thigh. Never did get to feel those legs wrapped around him, but. Well. “You really from out of town?” he asked. Didn’t mean it to be a whisper, but it was.

A nod against Dean’s shoulder. Just the slightest hint of a sigh again, like one getting held in, but with them pressed so close he could feel it. When he whispered, “I should go,” it didn’t feel like a lie. Or an excuse.

Dean hesitated, stared at the dim outline of the door across the room. He didn’t do this kind of shit. But he’d kick himself if he didn’t say it. “Hey, um. If you’re in town again, look me up, ‘kay?”

A brief hesitation behind him, and Dean would have actually, physically kicked himself if he’d been able, “I… yes. If… yes. Alright.” Soft lips pressed to the line between Dean’s neck and his shoulder, sensitive now with the rasp of stubble. Then again, almost shyly, “Before I leave… may I…?”

There it was again, and Dean blinked, then chuckled. He’d fucked Dean into being a walking wet spot and he was still asking for permission. Holy cute, Batman. “You and your ‘May I,’” but even he could hear how fond it sounded. “What?”

There was a shifting of weight behind him, pulling up and over with that just slightly tacky feeling of skin on skin, and then arms were framing Dean’s body, nudging him back onto his back. Dean reached up and trailed his fingers through that sex-messy hair—really sex-messy now, not just fucked up—and down the curve of a slanted jawline, traced the tight line of lean, fit shoulders. Couldn’t help his smile as he admired the way that even now those blue eyes were a bit uncertain but the determination in them was still so intense. Damn. 

He’d miss this guy.

“I would like to suck you again,” the accountant said, soft, seriously. “Get you erect in my mouth, take you to orgasm, this time. I would like to know how that feels.”

What?

Dean hadn’t actually known that at his age he _could_ get it up again that fast. They both looked down and almost bumped heads as Dean’s dick said hello right at the guy’s groin. Okay, so much for getting hard in his mouth.

Seriously. Fucking. _Awesome_.

“Y’know, I kinda thought you were gonna ask for a kiss,” Dean muttered, dumbly.

“Oh,” some six feet of ridiculous, unexpected gorgeous hovering over him blinked, once. His smile at that was so shy it pinged at Dean’s ribs. “I would like that, too.”

After, with Dean’s knees still wobbly and his pretty boy’s lips swollen and looking about as smug as could be, they did end up kissing at the Jeffrey’s door—and holy crap Smoke was right, that beige coat that was hanging limp and lonely up on the rack of the now-closed bar was _really ugly_. It was a good kiss, too. As good as the first. Better, even, lazy and easy and slow—not even any tongue, just a tiny scrape of teeth, tasting a bit like latex still. Not ‘nice to have known you,’ but ‘Hey, see you later.’

Even though, well, it wasn’t.

Yeah, no. In the end, Dean’s funny, weird little angel didn’t give away his name or his number.

But then, neither did Dean. 

*_*_*_*

“Charlie…” Dean warned, glancing at his watch. Two minutes. There was ‘too early’ and there was ‘right on time’ and there was ‘disrespect,’ and if the fucking Novak boy hadn’t accounted for the traffic going into the city, that didn’t speak well of him, Gabriel, their organization, or the night’s likelihood of not ending bloody. Dean did not think for a second that a guy who had managed to dodge Dean’s soldiers for a _full week_ wasn’t capable of arriving on time when he wanted to.

“Okay, _okay_ ,” Charlie was tapping frantically on the screen of her phone, her shoulders bunched up. Not that _Dean_ would ever have done anything to her, but he got her point, she was a fixer, she _fixed shit_ and that included fixing shit so they didn’t end up with an internationally-inspired Mafia war in the middle of the Midwest. She let out a big heaving, laughing breath. “Oh. Yeah, okay, so… they parked on the wrong side of Millennium and didn’t want to deal with the under-streets, they’re—oh!” She started bouncing briskly around the big shiny art fixture, Dean and Sam and Cole and Rufus trailing around behind her. Dean really didn’t want to be doing too much more walking today but the job was the job. “They’re coming from the _other_ side.”

Sam’s lips were twitching, though, and he nudged Dean, chuckling. “I think Rufus is disappointed,” he murmured. “Says Bobby hasn’t let him shoot anyone in too long.”

Okay, so maybe the fact that Charlie had had them meet in a really, really, _really_ public place wasn’t _just_ because the Russians had a hella violent reputation. Rufus was one of those enforcers who really earned the old term ‘torpedo,’ and he was just too ornery to die, and too mean to get killed. Dean thought he was _hilarious_ . And Cole had a bit of a trigger finger sometimes and a chip on his shoulder the size of the Willis Building but he’d heel if Dean and Sammy told him to. Mostly. Came with the whole time he’d decided _he_ needed to be street boss, and yeah, that’d gone about how everyone had thought it would.

The Russians were all wearing suits as they strode up from the inside of Millennium Park, Charlie waving to them as if she’d just arranged for a bus tour of the city. Fucking _suits_ . Oh, yeah, _real_ subtle there. Even in the dim street lights the four of them looked like _crows_ flapping down the long pedestrian path. Dean bit down on his lip in amusement and stepped around the curved edge of the Bean, Sammy at his shoulder.

The guy at the front caught Dean’s eyes and stopped dead right in front of the three little stairs leading up to the Bean’s viewing platform. The only reason his own men didn’t run right into his back was that they were walking at least a few steps deferentially behind, and the beige edges of a too-large, ugly trench coat flipped and flapped behind him in the sharp spring wind. Everyone stumbled to a stop. 

Big eyes with sad corners were wide and dark, too dark to see their blueberry color from here, and full cotton-candy pink lips hung just a little open in a way that made the soft bowed dip in the top one very obvious.

Dean didn’t pretend inside his head that that reaction was ‘cause Dean Winchester was intimidating as all fuck when he wanted to be. Not this time. He wasn’t pretending anything on the inside of his head right now, ‘cause all up in there was white and shadows, stinging bright, the shadows of the Jeffrey’s back room and clean white sheets and a cock in his ass, careful shaky comedown kisses across the back of his neck.

He hadn’t been so shocked the last time he’d been _shot_.

“Um, I… hey, you guys are right on time! Right, Dean?” Charlie laughed into the thick, uncomfortable silence, and even her normal laughter sounded a little strained. “Well well, the gang’s all here, thank you for your services and… uh, yeah, I’m gonna…” out of the corner of Dean’s eyes he could see her looking back and forth between them and backing away slowly, one hand out in front of her. Dean couldn’t even blame her, blame any of them for that reaction, everyone was watching him, tense and ready to take his cue—

But Dean didn’t watch her go, he couldn’t tear his eyes off either, because how the Hell was this his _life_?

“Oh,” said the hot accountant who’d fucked him right into next week then sent him on his way with his legs still shaky from a goodbye blowjob and a slow kiss so sweet that it’d raised Dean’s goosebumps and melted his knees. “Are you…” and then he trailed off, straightened. Lifted his chin high as he mounted the stairs, straight-shouldered, pink lips pitched into a serious line, and the familiarity of all _that_ burned like a shot of Bobby’s rotgut. “I’m Castiel Novak,” he finished, and there was no break in the gravel voice now.

Yeah, there’d been no way he could be anyone else, no way at all, but oh, fucking _shit_.

“You don’t have an accent,” Dean blurted out, because he was just smooth like that, and he didn’t even have to see him to know that Sammy had just tensed further, because _everyone’s_ hackles had just risen like a set of cats out to throw down. In the sudden rattling quiet of the streetlights and Millennium Park after dark, he heard the soft hiss of something that Dean did not have to understand to know that it was definitely not complimentary from one of the cliché suited goons standing just behind and to the side of Castiel. 

Oh, right, insult the Russian mobster from a centuries-old Russian mob family by implying that he _wasn’t Russian enough._ Jesus Christ in a tiny canoe Dean Winchester, maybe Rufus was gonna get his wish after all. If the Russians didn’t kill Dean, Bobby would.

Castiel blinked, slowly, then eyed him up and down like he was looking for that screw that Dean was missing. Which Dean could not blame him for because what he’d said had been _fucking stupid._ But—a little to Dean’s surprise—the corner of that full pink mouth turned into… was that a smirk? “Neither do you,” he finally answered.

“I was born in _Kansas_ ,” Dean didn’t even know why he felt he had to point that out.

“I was born in _Brooklyn_ ,” Castiel shot back, and yeah, that was definitely a smirk now. “You will keep your foolish prejudices about my Bratva and my family to yourself.”

Yeah, that, that was definitely _not_ respect, and there was a soft click as Cole thumbed off his safety.

The moment hung, and hung, sword-bright in the reflected nighttime light off the Bean, and this time, Dean was the one who broke it. 

He puffed out a laugh. “Guess I’d probably sound pretty ridiculous with some old-school mob accent, huh?” Felt the bristling tension release from his back, from Sammy’s, saw the at least temporary cease-fire snap into place between them. The three behind each of them were still eyeing each other warily—Sammy could do a mean bitch-face like no-one’s business, the little Asian dude Castiel brought with him was looking scared, and he _should_ —but no-one had any weapons out or imminent. “I’m Dean Winchester.”

“Yes, I’d gathered,” dry, so very, very, very dry. 

“Yeah,” Dean grunted, and kind of waved a hand. “You wanna tell me why you’re in our city?”

The smirk settled down, that expression was flat and calm again, only the uneven tie and the edge in those blue eyes making him look like anything but a slightly ticked-off representative of the IRS. “Gabriel has a proposal for Robert Singer.”

Ah. _Ah-hah._ There were the puzzle pieces. Of course Gabriel couldn’t come himself, because that’d put him in the position of having to come to Bobby, so that was why he’d sent his second. And of _course_ Castiel, the little sonofabitch, had given them the runaround the whole week, ‘cause if someone from the Brotherhood was gonna come to them he was gonna prove he was doing it on his own damned terms and they couldn’t make the Bratva do a fucking thing they didn’t want to, even in their own city.

Play ball, indeed. Well, Dean could play this one like a Cubbie.

“Pretty sure Bobby’s already married,” Dean answered. Just to see what he could get. Sam didn’t _quite_ huff ‘Deaaan’ behind him, but he definitely wanted to.

Even with the coat and the suit hiding so much of his body language, that eyeroll of Castiel’s occupied eyes, chin, and shoulders, and was, if Dean was gonna be honest with himself, really fascinating. He normally actually liked this part of the dance, liked this feint and jab just as much as he liked it when he was boxing, just as much as he liked foreplay—

Okay, whoa there Winchester.

“Kevin has the letter,” Castiel clearly was so done with Dean’s bullshit, which was fine, that was just _fine_. Those blue eyes left his face—and actually, now that Dean thought about it, it was nearly the first time they had—to nod behind him at the young guy who looked like he was about thirty seconds from clutching at his pearls. “I see Sam Winchester is here as well, they can discuss financials.”

“Kevin. Oh. Wait. _You’re_ Prophet _?_ ” they really had gone for symmetry, here—Dean had brought Sam, as the Outfit’s current _consiglieri_ —he would have anyway, Sammy was badass if there was a fight but it was always helpful to have a lawyer on hand if there was the possibility that the police was gonna end up involved in a public place. And Castiel had brought Kevin “Prophet” Tran, who was, well, whatever financial advisor to the Bratva’s head was in Russian. And probably was _not_ badass in a fight. Dean didn’t know what he’d been imagining out of the Brotherhood’s main money guy, but it sure as Hell wasn’t a kid that hardly looked old enough to shave, and that Sammy could have probably bent in half like a pretzel. What did Dean know, though? Death and taxes and all that.

They stepped away, leaving Sammy side-eyeing Kevin mistrustfully as they looked around, found nowhere where there could be any privacy—because there wasn’t any—and ended up stepping underneath the Bean’s center arch, the span of mirrored metal just barely tall enough that it cleared Sammy’s head. Which left Dean and Castiel just staring at each other, their reflections doing the same. 

Dean’s shoulders ached, and it was pretty sure it was with tension this time and not the memory of hands on his hipbones hard enough to bruise, kisses on the knob at the base of his neck. 

But…

 _He didn’t know_ . The shock that had washed over Castiel’s face when Dean had rounded the corner hadn’t been feigned—hadn’t needed to be. It’d probably been just as obvious as the shock that had been on _Dean’s_ , and what their respective guys had made of any of that he just didn’t know either. Too many fucking _unknowns,_ and the biggest one had his hands in the pocket of an ugly beige trench coat and still didn’t know how to tie a tie.

But that was neither here nor there nor goddamned _anywhere_ , and right now the ache in Dean’s thighs and ass or the way the guy’s—Castiel’s—teeth had just barely brushed on the inside of his lower lip before they’d parted, yeah, all that mattered for _fuck all_. So when he sauntered forward to stand just in front of Castiel, watching the way his shoulders just barely ramped up and his chin raised, hands coming out of his pockets. When Dean turned to give him his side, facing the reflective metal of the Bean like the lights of the skyline and the very faintly orange-tinged sky were the most fascinating thing he’d ever seen, it was every bit cock and balls and sass, ‘cause that was the Dean Winchester game and no-one played it better than Dean himself.

Castiel didn’t go for a weapon at Dean’s approach—he’d known he wouldn’t, ‘cause that would have meant that he considered Dean a threat. But he also didn’t move where his hands were hanging at his sides to fold them, didn’t put his hands back in his pockets. Instead, slowly, he turned, too, watching their reflections—the way Dean knew those shoulders were broad under the jacket and the coat, which _was_ big enough to have a hand-cannon sawed off under it; the white, cleanly pressed dress shirt, the tie that still had its knot located somewhere around Castiel’s third button…

Dean cleared his throat. “Hey, why do you tie your tie like that?”

The rasp of the answer gave him nothing—well, nothing but a sweet little chill of familiarity up Dean’s back that he swatted like a July mosquito. “It’s not a slip knot and it isn’t against my throat,” cool and cold and confident that the information couldn’t be used against him. “So it can’t be used to choke me without significant maneuvering.”

“Oh.” But that was all Dean could actually think of to say. More questions crowded behind his teeth and he swallowed them, because they had nothing to do with anything, including the fact that either Castiel was halfway to Narnia or the Bratva had really changed their position on some of their shit. Yeah, _Dean_ was out, but that Gabriel’s little brother, his Parakh, Dean’s own parallel in Brighton Beach Little Odessa, definitely had a thing for cock? Even if Dean hadn’t been the _owner_ of said cock he’d’ve been kinda floored.

“It’s my first time in Chicago,” Castiel said, apropos of nothing, not even looking at Dean. Dean glanced, just quickly, at the plane of a cheekbone—Castiel’s eyes were raised upwards, and he honestly was looking at the triangle of light that was shimmering just above their heads. “It’s quite beautiful. Bewildering.”

“Uh-huh.” This was what they were doing? Small talk? Except Castiel apparently hadn’t gotten any better at that in the last, oh, fifteen hours either, so he trailed right off on that and they kept on standing next to each other in awkward silence. From behind the Bean the cars rolled past with the whir of engines, but other than that only the streetlights buzzing and Sammy and Kevin talking quietly under the shadow of the enormous art structure made any noise.

“I’m truly curious as to why the Chicago administration thought that Chicago needed a giant distortive kidney bean, though,” Cas mused, finally, chin still tilted up to look at the shining curved surface, softer now, still in that voice that made Dean rattle around inside himself.

Dean’s first instinct was to bristle. He loved Chicago, this was his place, this was his _home_ , and this asshole and his people had still sauntered into _their_ territory without so much as giving notice. But… “S’called the Cloud Gate,” he answered, instead. Because, well, fuck it, it _was_ a giant distortive kidney bean, and no, he hadn’t missed that Castiel had said ‘distortive’ and not ‘reflective.’ The nerd. 

Blue eyes caught Dean’s in the mirror surface, black now in the orange-yellow lights of skyscrapers around them. One corner of his mouth curved upwards in a small, wry smile that shouldn’t have been familiar, but it was, it really was. “I know. I was at the Art Institute yesterday.” 

Before he’d gone to Jeffrey Pub.

Dean stared. Okay, definitely a nerd. Never mind that the guy was the Parakh to fucking _Gabriel_ , and came with a rep that made _sense_ now with the heat he was packing underneath the suit, and no, Dean didn’t mean the guns or knives or grenades or whatever it was he had in the inner pockets of that trench coat.

Also, that… kind of explained how Dean’s guys had lost him, what kind of self-respecting Bratva went to peer at Van Gogh’s smug mug in the tourist-littered art museum of a not-entirely-friendly city?

“What, you gonna tell me you took a Skyline cruise the day before?” Dean joked. The tour barges that floated down the river downtown and nattered on and on about the Chicago architecture as they maneuvered under the Adams and Wabash and LaSalle bridges had their ads with cheesy slogans and reports of five-star Tripadvisor reviews up all over the city.

“No.” Then, “It was raining. Two days ago, though.”

Dean stared, and this time, when he started laughing, he wasn’t sure he was gonna stop.

One of the guys behind Castiel called out in a ruffled growl—yeah, yeah, he wanted to light Dean up for his disrespect, sure, Dean didn’t even need to know Russian to understand that—but they couldn’t see Castiel’s face, the smile that crinkled at the corners of his eyes. And, more unexpected, one of those amazing eyerolls in response to the question that moved all the way from shoulders to messy hair. He raised a hand and waved them off with a single, _very_ Russian, flick of his wrist.

Dean settled in, pushing one hand into a pocket and letting his hip cock outwards, grinning. “What’s that your guys call you? Since your big brother, he’s the Novak, right?”

“Castiel.” Oh, now, that tone didn’t invite any questions.

Dean had never been good at taking any orders except ones he wanted to. His eyebrows rose. Even he knew the Russians really liked their nicknames. “Then your name sounds _really different_ in Russian, ‘cause that wasn’t what that sounded like. That a title or something? Ahnyal? Ahnye—”

“Aнгел,” Castiel finally muttered, and there was something about the way about his jaw tightened—it was too dark to tell if there was color rising to his face, Dean realized, not under his scruff, but if he put his hand on that high cheekbone would he feel it?

Yeah, that was when Dean realized, and threw his head back and laughed. “No. Oh, no. Oh, _fuck_ , please tell me that doesn’t mean what I think it does, Cas.”

Castiel’s chin tilted towards Dean, the skyline’s reflection across the Bean left fingers of light touching those amazing, soft pink lips, and his eyes narrowed.

Dean studied the look that wasn’t quite a glare and wasn’t quite a question pointed at him and picked back across what he’d just said. Huh. “No-one ever call you Cas?” he inquired.

“No.” Very strong hint there of ‘they wouldn’t dare.’

“Well, I like it,” Dean announced, just to be a shit.

But Castiel didn’t rise to it. “Do you?” Blue eyes fixed on his face, skimming the line of his cheek and his lips in a way that clenched Dean’s teeth around the effort not to growl or whine or _something,_ ‘cause this asshole was not allowed to give him a hard-on right in the middle of Millennium Park, right in front of Dean’s own damned guys. “You may have it, then,” he said, like a decision.

Dean was pretty sure he’d have kicked the guy’s ankle if not for the fact that one of the trigger-happies back there really might shoot him. “What the fuck is wrong with you? Stop flirting and _behave_ , goddammit.”

He’d said that louder than he’d meant to. The words hung there in the still, cold April air. Yeah, there was no excuse for that. Dean knew how to play this game better than this, he was just so fucking _off balance_ right now—how respect was perceived between families like theirs was about a hundred and ten fucking percent, and he might’ve just ordered one of the bosses of a violent, dangerous organization with whom he and his were on very shaky territory to submit to him. 

The veiled amusement left that pretty face so fast it left Dean dizzy. The corners of Castiel’s lips slanted downwards, just slightly, more of a threat than the tightening of his shoulders, and all of a sudden the dorky accountant was _gone_. He tipped forwards, near, too near, and Dean’s adrenaline rose so fast it left the Bean skimmed by a thin pale mist. 

Dean let his weight press onto the balls of his feet and wondered if Castiel had as many knives on him as Dean had. Probably. They’d see which of them was faster. And suddenly, unexpectedly, that thought made him so horny it _hurt._

Then Castiel “Angel” Novak _smiled,_ small and slow, and leaned close. 

And in his dark whiskey voice, whispered, “Make me want to.”

~fin~

**Author's Note:**

> “Aнгел” is pronounced [ˈanɡʲɪl] in IPA, and both translates and transliterates to ‘angel.’ I swear there was a thought somewhere about Cas and Dean actually having a conversation about their, you know, actual Mafia families, but they wanted to flirt instead, what can you do.
> 
> I love Chicago, and I honestly love the Bean, even if it is ridiculous. Jeffery Pub is a real place in the South Shore neighborhood; it is one of the oldest LGBT friendly bars in Chicagoland. It does have drag shows and the like, but on most other nights is a completely laid-back place, and Smoke Thompson is a real bartender there! That said, I have no idea if it has such a room in the back.
> 
> I also love the idea of them switching it up, so there might, someday, have to be a sequel. For plot purposes. Of course.


End file.
